This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R.sub.6 is H or alkyl; or PA1 R and R.sub.6 can be taken together to form --(CH.sub.2).sub.4, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --. PA1 R.sub.6 and R may be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 -- or ##STR12## provided that when R is OCH.sub.3 or OC.sub.2 H.sub.5, then R.sub.6 is H or CH.sub.3 ; when R.sub.6 is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN, then R is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN; R and R.sub.6 have a total number of carbon atoms .gtoreq.13 and that when NR.sub.6 R is other than NHOCH.sub.3, NHOC.sub.2 H.sub.5 or ##STR13## then R.sub.2 is NCO, NHC(O)B, NHC(O)SB.sup.I, NHC(O)OB.sup.II, NHC(O)NHB.sup.III, CF.sub.3 SO.sub.2 NH or CH.sub.3 SO.sub.2 NH. PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3 or NO.sub.2 ; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 is ##STR15## X is CH.sub.3, OCH.sub.3 or Cl; Y is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 Y.sub.1 is H, Cl, CH.sub.3 or OCH.sub.3 ; and PA1 Z is CH, CCH.sub.3 or N PA1 (1) the bond between N--R and A is attached to a nitrogen or carbon atom of A; PA1 (2) when A is a thiophene or furan ring, the bond between NR and A is not at the 2- or 5-position of the heterocycle; and PA1 (3) when X is Cl, then Z is CH and Y is CH.sub.3, OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2. PA1 (1) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered aromatic heterocycle containing one to three nitrogen atoms; PA1 (2) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered dihydroaromatic heterocycle containing two nitrogen atoms; PA1 (3) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one to four nitrogen atoms; PA1 (4) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one or two nitrogen atoms and one oxygen or one sulfur atom; PA1 (5) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one oxygen or one sulfur atom; PA1 (6) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered dihydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur; PA1 (7) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered tetrahydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur; PA1 (8) Compounds of Preferred (1)-(7) wherein ##STR16## Y is CH.sub.3 or OCH.sub.3 ; and Z is CH or N; (9) Compounds of Preferred (8) wherein A is unsubstituted or optionally substituted with 0-4 CH.sub.3 or 0-2 OCH.sub.3 groups; PA1 (10) Compounds of Preferred (9) wherein A is a pyridine, a pyrimidine or a 1,3,5-triazine; PA1 (11) Compounds of Preferred (9) wherein A is a pyrrole, an imidazole, a pyrazole, or a 1,2,4-triazole; PA1 (12) Compounds of Preferred (9) wherein A is an isoxazole, an oxazole, a 1,3,4-oxadiazole, a thiazole, a 1,2,3-thiadiazole, or a 1,3,4-thiadiazole; PA1 (13) Compounds of Preferred (9) wherein A is a 4,5-dihydroimidazole, a 4,5-dihydroisoxazole, a 4,5-dihydrooxazole, a 4,5-dihydropyrazole, or a 4,5-dihydrothiazole; PA1 (14) Compounds of Preferred (9) wherein A is a tetrahydropyrimidine, a tetrahydro-1,2,-oxazine, a tetrahydrol, 3-oxazine, or a tetrahydro-1,3-thiazine; PA1 (15) Compounds of Preferred (10)-(14) wherein R, R.sub.1, R.sub.2 and R.sub.3 are H, and A is unsubstituted, or, optionally substituted with one methyl group.
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR2## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR3## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR4## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR8## wherein R=H or CH.sub.3.
Unexamined European Pat. No. 7687 discloses, among others, herbicidal sulfonylureas of the general structure: ##STR9## where R is H, alkyl, alkenyl, aryl, etc.;
U.S. Ser. No. 209,307, filed Nov. 24, 1980, discloses, among others, herbicidal sulfonylureas of the general structure ##STR10## where R is H, C.sub.1 -C.sub.12 alkyl, --(CH.sub.2 CH.sub.2 O)--.sub.n'" R.sub.12, CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.12, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.5 -C.sub.8 cycloalkyl substituted with 1-3 substituents selected from 0-2 OCH.sub.3, 0-3 CH.sub.3 or C.sub.2 H.sub.5, trifluoromethylcyclohexyl, C.sub.4 -C.sub.10 cycloalkylalkyl, C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 CH.sub.3, CH.sub.2 CH.sub.2 CN, C(CH.sub.3).sub.2 CN, OCH.sub.3, OC.sub.2 H.sub.5, N(CH.sub.3).sub.2, ##STR11## R.sub.6 is H, C.sub.1 -C.sub.3 alkyl, allyl, CH.sub.2 CN or CH.sub.2 CH.sub.2 CN; or
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.